This event is an extreme version of the event, Long Jump, as characters sprint off a track and fly through the air. The goal of this event is to fly the farthest before landing. However, characters must land on an island; falling into the water will result in a foul. The wind becomes a factor in speed and movement of the participant.

Dream Long Jump appears in the Wii version of this game as well, now taking place at Yoshi's Picture Book from Yoshi's Story. The game involves players jumping on clouds to see how far they can travel before falling into the water. Falling off the stage results in elimination. Results are given after the final player falls off.

During the event, several giant Bullet Bills and Big Cheep Cheeps will appear and attack the competitors. Fly Guys, balloons and Cleaving Clouds that split or disappear when Ground Pounded also help the players to jump through the course. After a player loses, they become flying bombs balloons and are able to push other players who are still competing.

During London Party mode, when the player faces off against Dry Bowser, they compete in the Dream Long Jump event.